We absolutely wouldn't end up in the same place, simply because the state space of possible organisms and environments is astronomically larger than the space of possible dice rolls (his metaphor isn't perfect and I'm already straining it here). But we would be almost guaranteed to end up with organisms that have similar levels of complexity.

Again, randomness is an important part of evolution, but there are also necessary deterministic aspects of it that make the "blind watchmaker" type arguments that started this discussion irrelevant.